Triethylsilane → HCID 117667417, compound

HRID 1526260Notes

Reaction equation

HRID 1526260 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][CH:25]([N:28]4[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]4)[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[C:5]([C:12]([NH2:14])=[O:13])=[N:6][C:7]=1[C:8](O)([CH3:10])[CH3:9].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[Cl:1][C:2]1[N:3]=[C:4]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([N:22]3[CH2:23][CH2:24][CH:25]([N:28]4[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]4)[CH2:26][CH2:27]3)=[CH:20][CH:21]=2)[C:5]([C:12]([NH2:14])=[O:13])=[N:6][C:7]=1[CH:8]([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 88569772HCID 88569772, compound

Product 1

HCID 117667417HCID 117667417, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a mixture of 5-chloro-6-(2-hydroxypropan-2-yl)-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (11.2 g) and trifluoroacetic acid (110 mL) was added triethylsilane (18.2 mL) under ice-cooling, and followed by stirring under ice-cooling for 10 minutes and at room temperature for 14 hours. The reactant was concentrated, then diluted with chloroform, and washed with a saturated aqueous sodium hydrogen carbonate solution. The organic phase was dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The residue was purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous ammonia=1:0:0-500:10:1) to obtain an orange solid. The obtained solid was heated and washed with ethyl acetate to obtain 5-chloro-6-isopropyl-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (9.2 g) as an orange solid.

Workup

  1. temperaturecooling
  2. concentrationThe reactant was concentrated
  3. additiondiluted with chloroform
  4. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous ammonia=1:0:0-500:10:1)
  8. customto obtain an orange solid
  9. temperatureThe obtained solid was heated
  10. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-1028f1b526c043dfa5b79c798b2be64f
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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